alpha-Methylserotonin

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α-Methylserotonin
5-HO-AMT structure.png
Systematic (IUPAC) name
3-(2-aminopropyl)-1H-indol-5-ol
Clinical data
Legal status
Routes Oral
Identifiers
CAS number 304-52-9 YesY
ATC code None
PubChem CID 2107
IUPHAR ligand 152
ChemSpider 2023 YesY
ChEBI CHEBI:48295 YesY
ChEMBL CHEMBL275854 YesY
Chemical data
Formula C11H14N2O 
Mol. mass 190.242 g/mol
 YesY (what is this?)  (verify)

α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a tryptamine derivative closely related to the neurotransmitter serotonin (5-HT). It acts as a non-selective serotonin receptor agonist and has been used extensively in scientific research to study the function of the serotonin system.[1]

Unlike serotonin, αMS is not metabolized by monoamine oxidase on account of the α-methyl substituent blocking the enzyme access to the amine. As a result, it has a much longer half-life in comparison.[2][3] Similarly to serotonin however, αMS poorly crosses the blood-brain-barrier due to its free hydroxyl group, and thus has only weak or no central effects when administered peripherally.[2]

α-Methyltryptophan (αMTP) is a prodrug to αMS which does cross the blood-brain-barrier and thus efficiently delivers αMS into the central nervous system.[4][5] As a result, αMTP acts as an orally bioavailable false or substitute neurotransmitter for serotonin, and has been suggested as a possible therapeutic agent in the treatment of disorders where serotonin is deficient.[4][5] The O-methylated analogue of αMS, 5-MeO-αMT, also readily enters the brain and could be used for this purpose as well.[2][6]

Legal status[edit]

United States[edit]

5-Hydroxy-alpha-methyltryptamine is not scheduled at the federal level in the United States and is therefore legal to buy, posses, and sell.[7] It is possible that 5-HO-AMT could be considered an analog (of AMT), in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analogue Act.

Florida[edit]

5-Hydroxy-alpha-methyltryptamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[8]

See also[edit]

References[edit]

  1. ^ Ismaiel AM, Titeler M, Miller KJ, Smith TS, Glennon RA (February 1990). "5-HT1 and 5-HT2 binding profiles of the serotonergic agents alpha-methylserotonin and 2-methylserotonin". Journal of Medicinal Chemistry 33 (2): 755–8. doi:10.1021/jm00164a046. PMID 2299641. 
  2. ^ a b c "Erowid Online Books : "TIHKAL" - #48 a-MT". 
  3. ^ Diksic M, Nagahiro S, Sourkes TL, Yamamoto YL (January 1990). "A new method to measure brain serotonin synthesis in vivo. I. Theory and basic data for a biological model". Journal of Cerebral Blood Flow and Metabolism 10 (1): 1–12. doi:10.1038/jcbfm.1990.2. PMID 2298826. 
  4. ^ a b Sourkes TL, Montine TJ, Missala K (1990). "Alpha-methylserotonin, a substitute transmitter for serotonergic neurons". Progress in Neuro-psychopharmacology & Biological Psychiatry 14 (5): 829–32. doi:10.1016/0278-5846(90)90055-l. PMID 1705718. 
  5. ^ a b Sourkes TL (1991). "Alpha-methyltryptophan as a therapeutic agent". Progress in Neuro-psychopharmacology & Biological Psychiatry 15 (6): 935–8. doi:10.1016/0278-5846(91)90020-2. PMID 1763198. 
  6. ^ "Erowid Online Books : "TIHKAL" - #5. a,O-DMS". 
  7. ^ §1308.11 Schedule I.
  8. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL